Interview with Gary Gulman
Thursday / October 1, 2026
About Gary Gulman
American stand-up comedian who started in Boston in the early 1990s. Known for Last Comic Standing, the HBO special The Great Depresh and the solo show Grandiloquent.
Source: Mike Birbiglia on YouTube
These answers are taken from Gary Gulman | Mommy, Look! | Mike Birbiglia's Working It Out Podcast on Mike Birbiglia's YouTube channel. You! Backstage did not conduct this interview.
What was your very first experience with comedy?
I said that just about every one-person show could be called Mommy, Look. But I also feel that every standup show that I've given over the past 30 years, the subtext is Mommy, look. It's an audition for an audience of one, in some ways. It's certainly where I started. Mommy, look, that's how I started performing. When I wanted to be a comedian, my mother said, you don't make us laugh.
When I first saw Dane Cook, I was 22 years old and going to my first open mic. I didn't know anything about him or his trajectory. I just remember he made these people go crazy with how funny he was about Speak & Spell and Jurassic Park, and he's 18 or 19 years old. Here's the thing that you have to avoid in early comedy: seeing somebody who makes you want to quit.
The original way most of us start off, there was this guy, Chuck Martin, who said he thought when he first started doing comedy that it was just Snappy Answers to Stupid Questions from Mad Magazine. In Boston it was always the witty things they said to police officers arresting them for drunk driving, and that would murder at the comedy shows in Boston in the early 90s when I started.
What do you enjoy most about comedy?
Making friends after 40 is really tough, because we're so set, and we have our own friends and usually our partners, so it's difficult to fit them in. But I've been pretty good about making some good friends after 40, and it's easier when you're a comedian, because you have more free time than most people, and you're intersecting with newer people from time to time when you work on new projects. And also the diversity of the types of people that we intersect with. It's like sports or music. We're really lucky.
A lot of fans can be very funny. I had a joke for months that the Sermon on the Mount was not improvised, that Jesus workshopped it. And a fan said, what about saying that he went to all the open mounts? I thought that was terrific, and I used it in the next show, and it got a laugh.
What advice do you have for new comedians?
This is the great thing that you learn as you get older: don't compare yourself to the other comedians. In your head you can make them all better than you. But compare yourself to yourself a year or two ago, or when you were working at your best creative level.
David Tell, and I heard this thirdhand or fourthhand, so who knows what he said originally, but he said you need a place where you can kill and a place where you can bomb. That's really important. You don't have to bomb in the places that you can bomb. You just have to go with that feeling. For me, for a while, it was the original Comedy Studio in Cambridge, above the Hong Kong, and now I feel like it's QED and Union Hall.
I remember one night not being very entertaining at the Cellar and getting a phone call about my lack of entertaining. I was very careful about what parts of The Great Depresh I shared at the Cellar, because some of it is a bummer, some of it is not all that funny, and some of it was not worked out entirely.
Who is your favorite comedian, and why?
Norm Macdonald was one of the best at going really, really general. A lot of the things he said were basically just the simple truth, and he wasn't really putting much on it. He was a really great executor of understatement and overstatement. He would say things like, Hitler, we should be worried about that guy.
I couldn't watch too much Brian Regan, because there was always this thing where I was like, why do I even bother? It's being done better, more physical. And when I watch Chris Fleming now, I'm like, man, is he bringing everything into every joke. Why is anybody else doing comedy, because he's got it so locked down. He's so original and fun and joyous and smart. And also the way he moves I'm envious of. And he's a great dresser too. At 54, I can't wear a boa, even if I wanted to.
Describe your style.
I think I was influenced a lot by the speed of Boston comedy, and the need for a male Boston comedian to be the coolest guy in the room. That's helpful in some ways and not helpful in artistic ways a lot of the time.
I want to write smart jokes, and so I work really hard on writing smart jokes. Good comedy is specific, specific. But every once in a while you go really general. You could probably take most of our jokes and say, well, this is understatement. But it's what we're able to do with it at this point in our decades-long careers to make it seem fresh or original. I always think about how the simple truth is frequently the funniest, and just saying something using the right words is so much of it.
I always try to imply to the audience that these are things I've thought of afterwards, and not things that I so wittily whipped off, because I think early in my career I implied that I was so witty, moment to moment. We're never as funny after the show as our perfectly constructed 60-minute monologue we wrote over the course of four years.
Tell me about a bit or a project that was hard to get right. What was it and why was it challenging?
The state abbreviations joke was in my notebook for 20 years. Until they started making documentaries about little things, there was really no way to tell it, or I didn't know the way to tell it. It's the thing I've been thinking about since third grade, when I got a book with all the state abbreviations in it, and I thought it's going to be really hard to memorize these, because most of these states start with the same first two letters. When you start doing comedy, you're spending all day thinking, is this funny? But the premise isn't strong enough to hold the rest of the joke.
Here's what was difficult: anytime you say anything good about Millennials at the average comedy club, they're so conditioned from comedians bashing Millennials that they think you're being sarcastic. So it was always a fight against that. They are kinder on the average and more empathetic than we are, and much less tolerant of bullies and homophobia. Once you have 'they'll get some practice,' all you have to do is come up with what the practice will be. You can go truly specific, but it's not as funny as the broader, which is counterintuitive.
Tell me something I may not know from reading your credits.
I repeated the first grade, and a lot of what I became soon thereafter, and what I am now, is based on that. I didn't have a friend until fifth grade, and so I had high ideals for friends, but I also attracted loyal friends, because it doesn't take much to hurt my feelings and make me withdraw.
For a long time I didn't want to have kids. The main reason was that my childhood was such a nightmare that I didn't want to visit that on someone. But once I got healthy, I thought, no, life is a pretty good run. If somebody could have a life similar to mine, or at least the amount of joy that I'm able to experience from my mid-40s through now, I'm 54, I'm very positive about the prospects for a Gulman child.
My mother did say something really great. She said if you have one good friend, you're doing great. And also, you're never alone if you have a book.
Gary Gulman's Full Biography
Boston's Gary Gulman has appeared on just about every television show a young stand-up comedian can appear on, including The Tonight Show with Jay Leno and The Late Show with David Letterman. His brand of clever, original comedy has delighted audiences of all ages all over America. While Gary has been a headlining comedian for several years now, he is most well known for his breakthrough success on NBC's hit stand-up Showcase, Last Comic Standing. Over the past four years his charm and talent have also caught the attention of numerous television networks who have inked Gulman to star in lucrative comedy projects for them, including CBS, Showtime and FOX to star in his own show. Though he's only been performing for a relatively short time, his body of work includes a half-hour Showtime Network special, a critically lauded CD entitled Conversations With Inanimate Objects and a soon to be released one hour DVD from Goldhil Media entitled Boyish Man. Comedy experts everywhere praise Gary as one of the top comedians touring today.